Until then, it's a volatile situation with no safety margin and several challenges I need to overcome to ensure financial survival:Successfully fade any unexpected expenses from inspections or repairs with zero cash on hand.Arrange for rent increase or tenant removal in the least disruptive way possible.If tenants are removed, they will need to be replaced immediatelyMy brainstormed solutions so far are:Regarding unexpected expenses: Craig Curelop my unit by getting a futon and Air BnBing the rooms to increase cash flow or borrow from family.Regarding rent increase/tenant removal: use property management or letters? 

Writing a book on notes has a lot of variables to overcome.

There's plenty of guys in my town that spent more than 5 years locked up for their "creativity".If the sale history is public knowledge you need to put your salesperson hat on and find a way to overcome that topic with your buyers and either move past it, or find another buyer who can move past it.

Typically the only one of these objections we can overcome is the last.

One way to overcome this is to partner with someone who IS more knowledgeable.

I encourage you, if you haven't already done so, to apply his overcoming objections/complaints techniques and rebuttals, or listen to @Michael Quarles podcasts/youtube...he has some great content and live calls talking to sellers. 

Which is most likely why the agent hasn't gotten to it yet (It is really an exercise in futility often especially if there is over 50K to overcome).

Having deals under my belt was all I needed to overcome the age obstacle because now I could talk about the deals I've done and that immediately gets past the "who do you think you are, kid?"

What obstacles did you over come along the way, creatively?

Can't offer much advice on how to overcome the lack of confidence but as a guy that grew up with a mom that suffered from the same issues I just want to say it sounds like you're pointed in the right direction.